It sounds like a line straight out of the first scenes in Citizen Kane: “How many of his contemporaries would still be alive?” muses Jim Grogan, chief counsel for the state’s Attorney Registration and Disciplinary Commission. In this instance, Grogan is alluding to Harry J. Busch, doyen of the city’s legal community, who died October 12 after a Methuselah-like career that began at the outset of prohibition. Depending on who’s doing the arithmetic, he was either 97 or 101; his family opts for the former age, while Illinois Supreme Court records indicate the latter.

During his nearly 70 years as a lawyer, Busch, a lifelong Chicagoan, represented nearly every type of client. Politicians: Mayor Richard J. Daley. Gangsters: John “Jackie the Lackey” Cerone. Cops: the Chicago Police Department’s “Red Squad,” investigated by the state’s attorney for secretly spying on citizens in the early 70s. And his own brethren: countless lawyers brought up on professional misconduct charges. “The only thing he wouldn’t do was represent somebody accused of dealing in dope,” notes Illinois appellate court judge Warren D. Wolfson, Busch’s friend and protege. “He just couldn’t bring himself to do it.”

Impeccably dressed and relentlessly courteous, Busch simply loved to practice law. “Although he was an ordinary-looking guy physically, he had a wonderful voice, and he had a very fluid way of moving his body and hands,” explains Wolfson, who before he joined the bench in 1975 sometimes served as cocounsel with Busch. “You just kind of watched him. He was like a great conductor, like a Toscanini in the courtroom. He had a way of moving and sounding that commanded attention. He wasn’t a screamer and shouter, he wasn’t melodramatic, but people listened to what he had to say, and within a very short time he was in control of the courtroom.

“He also had a great insight into human motivations and desires, and he knew how to reach for them. He was a master of picking a jury: by the time he was finished, the jurors were his friends.”

Born December 14, 1898 (or was it 1902?), Busch grew up on the city’s west side. A 1922 graduate of Chicago-Kent College of Law, he launched his career later that year as a Cook County assistant state’s attorney, then crossed over to become a top criminal defense lawyer, building a reputation as one of the city’s quintet of “B-boys,” as Busch’s Sun-Times obit called them–successful defense attorneys whose surnames began with the letter B.

“I remember as a young lawyer, before I knew him,” recalls Wolfson, “I was sitting in a court, and it was kind of noisy and disorganized, and suddenly there was a hush, and everything was very quiet when this man walked in. And I said to the person next to me, ‘What’s going on?’ And the guy says, almost with awe, ‘That’s Harry Busch.'”

Busch represented “hundreds and hundreds” of clients, adds Wolfson, his final big-ticket case occurring in 1985, when he took up the sentence-reduction cause of mobster Joseph Lombardo. In December 1982, Lombardo, ex-Teamsters boss Roy Williams, and three other men were found guilty of conspiring to bribe then U.S. senator Howard Cannon of Nevada in an effort to manipulate legislation affecting deregulation of the trucking industry. Lombardo got 15 years. Busch’s subsequent arguments failed to persuade a judge that Lombardo deserved a break.

His enthusiasm, apparently, never waned. “When I joined the ARDC in 1979, he was old then,” says Grogan, “but it appeared that all pistons were firing.” Grogan’s organization, which fields grievances from the public against state lawyers, ran up against Busch in court even as late as 1988, when he would have been either 85 or 89. “And he was registered for the year 2000,” points out Grogan, “meaning that if he’d walked in here on October 1, he could have practiced if he’d wanted.”

Yet despite his longevity, despite his prominence, despite his marquee clients, Busch is probably best remembered for a freaky, fleeting encounter with legendary outlaw Tommy O’Connor that occurred 79 years ago. In truth it was little more than an egregious case of wrong place, wrong time. But during the intervening decades it has attained near-mythic status, inextricably entwining the pair in the public mind even though they never set eyes on one another again.

Late on the morning of Sunday, December 11, 1921, Busch, still in law school, puttered through the city not far from the Cook County Jail, located back then on West Hubbard. Seemingly out of nowhere, a man hopped onto his car’s running board. “I was driving north from the corner of Clark and Illinois,” Busch recounted in a 1993 interview with the Sun-Times. “Suddenly the isinglass is ripped open, and in comes Tommy with his cannon. He said, ‘Drive like hell, you SOB, or I’ll blow your brains out! I’m Tommy O’Connor!’ I drove!” O’Connor “proceeded to give me directions,” Busch continued, until he seized an opportunity to shake the fugitive: “I had a chance to jam into a factory wall, and I did. The last I saw of him, he was running toward an alley east of where I was.”

Although present-day accounts invariably refer to him as “Terrible” Tommy O’Connor, he was known as “Lucky” Tommy O’Connor back in the 1920s, when his sensational exploits screamed from the pages of the city’s numerous newspapers. He embodied both nicknames: “Terrible” because he likely killed four people, “Lucky” because he did virtually no time for his crimes. By age 30 the Irish-born thug had established a reputation as a fearless gangster who’d already beaten two murder raps and was the leading suspect in a third killing. When five Chicago policemen, including Sergeant Patrick (Paddy) O’Neill, sought to arrest O’Connor in February 1921, gunfire ensued, and O’Neill was mortally wounded. Convicted of murder, O’Connor was sentenced to die by hanging in the Cook County Jail.

But at around 9:30 AM on December 11–between three and five days before his scheduled execution, according to various sources–O’Connor, brandishing a pistol rumored to have been smuggled into the jail inside a sandwich, led a bold five-man breakout. First the prisoners overpowered and tied up several guards, and then three of them, including O’Connor, hightailed it to freedom. Moments later he was in Harry Busch’s car, loudly introducing himself.

Hundreds of cops armed with rifles immediately flooded the streets. A $3,000 reward, big money for the time, was offered. And yet O’Connor was never apprehended. While sightings abounded here, there, and everywhere–one yarn placed him back in Ireland, where he supposedly died in the Black and Tan nationalist uprising of the early 1920s–no one officially saw Tommy O’Connor again. He leapt from Busch’s running board straight into the popular mythos, helped along immensely by Ben Hecht, who contributed to O’Connor’s notoriety by depicting the prison escape in a Chicago Daily News column, in an original story for the silent 1927 film Underworld, and most famously in the 1928 stage play The Front Page.

Over the years O’Connor remained very much a wanted man. In fact the gallows intended for him–though packed away in the bowels of the Criminal Courts Building after the introduction of the electric chair in 1929–were not dismantled until 1977, when a judge finally ordered the rotting wooden structure destroyed. (Instead it was purchased privately; these days the disintegrating platform is on display at Donley’s Wild West Town in Union, Illinois.)

Busch’s brief dustup with O’Connor would dog the attorney even after his death, as attested by obits in the Tribune and Sun-Times, which, while acknowledging his distinguished and lengthy legal career, made it abundantly clear that he will forever be known as the last man to see Terrible Tommy O’Connor–that this ancient accidental encounter, much to Busch’s chagrin, had somehow come to define his life. The Tribune went so far as to recall his reaction when, in 1996, on the 75th anniversary of O’Connor’s escape, one of its reporters asked Busch about his 1921 tete-a-tete with the gun-toting cop killer. “My God,” the ninety-something Busch bellowed. “Will that piece of history never die?” Well, no. At least not before he did.

Art accompanying story in printed newspaper (not available in this archive): photo/Fred Stein-Chicago Sun-Times.